Wonder Tools

The hardest part of writing is the first 10 minutes. Get past that, and momentum kicks in.

Once you start scribbling a few sentences, you’re on your way.

Having gotten stuck and unstuck a lot over the past 325 weeks of writing this newsletter, I’ve found a few tricks that help. Pick one to try, and leave a comment to share what you do to get unstuck.

As a little experiment, I’ve made an Unstuck Studio page to accompany this post and to help you get unstuck playfully.

As Daniel Pink explains, starting comes first.

“Action precedes motivation, not the other way around.”

When I’m stuck, I dictate rather than battle my inner critic.

The critic assumes there’s a better word for whatever I’m typing. It urges my fingers to stop and wait. When I’m rambling with my voice, the critic is quiet.

We call an idea freeze writer’s block, not talker’s block. When we speak informally, ideas just flow. Because spoken words disappear into air, it’s easier to avoid self-editing. In a dictated draft, clunky first words are OK because they get us closer to what we’re trying to convey.

Tools I use for dictating first drafts

* Google Docs voice typing works in more than 100 languages. In English you can add punctuation verbally or say things like “new paragraph.” See more of my favorite Google Docs tips and tricks. Free.

* Letterly works well on mobile or desktop. In addition to transcribing, it can give you a summary, or format your text. (It’s now a free perk for paid Wonder Tools subscribers.) Free with limits, or $80/year.

* Wispr Flow lets me dictate into any app or site on my laptop or phone. It works surprisingly well even if I whisper, which helps around other people. I just double-tap my Mac function key and start talking. Free to start; $12/month for pro features.

* Lispr.ai is a reliable Mac option. It can also translate your dictation. Free.

Simple alternatives: iOS Voice Memos and Notes transcribe your speech for free. On Android, try Google Keep.

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The Most Dangerous Writing App erases your words if you stop typing before your timer ends. Choose a three or five minute sprint, or set a word target. Once you get the hang of it, your hands will keep moving. Edit later. Free

Ilys is an even more challenging way to force yourself to keep writing. It shows your typing just one letter at a time. When your session is over, you can review and edit your words.

Free for basic use. Sessions are capped at 808 words, which is more than enough for freewriting. A subscription is $11/month, but I don’t need the extras.

Mind maps help you focus on concepts and ideas, rather than piling words onto the page. Connect your ideas to one another visually. Put one word down. Add a picture if you want. Pretty soon you have an outline to build on.

When I’m writing something complex or juggling lots of ideas, mind mapping allows me to assemble the bones of a piece efficiently. Use Apple’s free Freeform app on iOS or Mac. Or try simple apps like Mindmup or Bubbl.us. Both are free for up to three maps. Miro and Mural, which offer more advanced design features, also give you three free boards.

Rather than using AI to write, ask it to interview you. Or push it to provoke you. I find that helps me surface my own thoughts.

Prompts to try

* “Interview me about this. Ask one question at a time. Push me for depth.”

* “Provoke me. Give me a controversial statement to respond to.”

* “Push me to sharpen my viewpoint by pointing out potential blind spots in the ideas I’m starting to write about.”

* “Ask me five intriguing questions about this. Don’t answer any of them.”

* “Act as a tough mentor. Give me five unconventional writing prompts to pick from ….”

* “Ask a surprising question I’ve not heard before …. Include a feasible writing target to complete in the next 10 minutes.”

This last tactic is tech-free.

* Grab a piece of blank paper.

* Fold it in half three times. You now have 8 rectangles.

* Challenge yourself to put one sentence or phrase into each of the boxes. Set a timer to repeat every minute. Move to the next box each time it rings. Eight minutes later, you have a bunch of sentences to build on.

Slogans tell us that discipline propels people toward accomplishments. That sounds logical. But when I’m staring at a cursor, discipline alone doesn’t clear the fog. These tactics do. What helps you get unstuck? Leave a comment. 👇

More writing tool recommendations

I subscribe to hundreds of newsletters. Most weeks I read only a fraction. These are the dozen free ones I turn to first, all written by humans, plus five bonus picks from two guests. Share your favorites as a comment below.

1. Dense Discovery by Kai Brach

The best curated email I get. I find interesting sites, stories, and ideas in each post. It’s also gorgeously designed. It has a 63% open rate, roughly double the typical newsletter. For a sample, check out the recent “Cynicism is not a strategy” issue.

2. NextDraft by Dave Pell

I abhor the frenzy of 24-hour news cycles. But it’s a pleasure reading Pell’s daily NextDraft. He summarizes the day’s most interesting stories with a warm sense of humor, avoiding the anxiety-provoking tone of nightly TV news. He always includes at least one offbeat story that’s fun to share. WTF Just Happened Today also serves up a clear, concise take on today’s top U.S. news.

3. Cool Tools by JR Raphael

I always learn something from Raphael’s posts. Instead of chasing tech headlines, he tests and explains useful sites and services. His separate Android Intelligence email catches me up on new apps outside the Apple world.

I also like Recomendo. The three contributors spotlight six useful things in each issue, from a fantastic site, book, or video to an unusual hardware tool or a helpful Reddit community.

4. One Useful Thing by Ethan Mollick

The most insightful AI newsletter I read. Mollick, a Wharton professor, shares practical AI experiments with his 480,000 subscribers, testing what the tools can and can’t do well. Every few months he writes an opinionated guide, like this guide to which AI platforms you should try. His latest post features an elaborate music video he had Claude compose with Suno. His book Co-Intelligence, published in April 2024, remains a helpful AI primer. I’m looking forward to his next book, Co-Existence, coming out October 20.

5. Hulry by Rahul Chowdhury

Chowdhury blends common sense with creativity. His recent post, 21 Productivity Hacks I’ve Picked Up Over the Years, is a good example of his straightforward, practical takes. Like Dense Discovery, his Hulry posts are full of well-chosen finds. Each issue has something handy or quirky that’s fun to read about.

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6. Popular Information by Judd Legum

The best example of an independent investigative journalist making the Substack model work. It’s completely free to read, supported by paid subscribers, with no ads. Legum aptly describes his project as “News for people who give a damn.”

His accountability scoops on corruption and injustice lead to change. They’re full of carefully reported details and regularly picked up by major news outlets. One example of his impact: in 2020, after his reporting about Olive Garden, its parent company started providing paid sick leave to about 170,000 employees across 1,779 restaurants.

7. Second Rough Draft by Richard J. Tofel

Read this excellent newsletter if you’re interested in the state of contemporary journalism. Having been ProPublica’s first employee and its president from 2013 until 2021, Tofel brings experience, expertise, and evidence to his posts. He’s warned that many of the nation’s for-profit metro newspapers are “going out of business in slow motion.” His posts show how and why that’s happening, while also offering insight into the nonprofit news world.

8. Dr Phil’s Newsletter by Dr Philippa Hardman

Not that Dr. Phil. Hardman, a Cambridge University scholar, shares research-backed insights about how AI affects learning and teaching. Posts feature clear charts, frameworks, and novel ideas about AI and education. One recent writeup I appreciated explored the research on whether AI-generated videos actually help people learn.

9. The Pink Report by Daniel Pink

I’ve never met Pink, but I learn from him every week. His weekly pieces work as brief classes in wisdom, like 30 cheat codes for life and six skills humans need in the AI era. I especially enjoy Pink’s reading recommendations, like 11 essential books for 2026 summarized in 12 minutes. He’s as skillful at writing hundreds of pages as he is at drafting short videos. His book When explores the best times to do things. Watch his YouTube videos for short versions of his advice.

10. 3-2-1 by James Clear

I like Clear’s brevity. Three short ideas, two quotes, and one question to ponder. The formula has worked well enough to attract 3 million subscribers, more than any other publication on this list. I wish he’d write another book, given how good Atomic Habits was.

11. Techmeme

I check Techmeme daily to keep up with tech news. Its headlines sum up what’s new with AI and tech and link to multiple takes on top stories. There are many tech portals and aggregators, but this one has remained in my rotation year after year.

Two newer alternatives: Set up custom scheduled reports with Claude or ChatGPT. List your favorite topics, angles or outlets to highlight/avoid, and how often you want it. If you prefer manual curation, use Mailbrew to assemble your own digest. (Read my take).

12. Nice News

When I feel worn down by the news, I turn to this sweeter space. It’s full of hopeful pieces, but not random raccoon GIFs. One recent piece celebrated medical research breakthroughs, while another was titled “‘16,648 Reasons to Live’: Paper Highlights the Power of Small Joys for Suicide Prevention.”

To add to my recommendation list, I invited James Potter to share two of his favorite newsletters. He runs Reletter, which tracks around 7 million newsletters across Substack, Beehiiv, LinkedIn, Ghost, and more.

Potter recently mapped how newsletters cluster based on the links they share (reletter.com/graph). He publishes a weekly ranking of the most-cited links. It’s a superb resource for keeping tabs on what people link to most.

13. Stratechery by Ben Thompson

James: I’ve paid for Stratechery since 2021. If I could only keep one newsletter it would be this one. Thompson writes about the business strategy behind tech news. Whenever something happens, he works out who ends up with power over whom. His main tool is a framework he calls Aggregation Theory, which says that whoever owns the relationship with users gets leverage over everyone supplying them. He’s great at weaving his past analysis into current issues and tying everything together.Recently he wrote an interesting article about the idea of AI agents doing your shopping for you. Walmart was one of the first big retailers to sign up for OpenAI’s Instant Checkout. Walmart pulled out a few months later because orders placed through ChatGPT converted at a third of the rate of its own site and app, and the baskets were smaller too.

14. Benedict Evans

I read Evans’s email every week. It’s how I catch up on anything in tech that I missed. I also like his way of seeing the world. He spent years as an analyst and was a partner at Andreessen Horowitz. Each week he picks the tech stories that mattered and adds a few lines of context to each, often with a dry joke. He’s good at checking hype against the numbers.

When SpaceX filed to go public, for example, Evans wrote about how xAI’s data center provides services to Anthropic for $15 billion a year, more than SpaceX’s entire launch business.

❤️ What newsletter do you like? Leave a comment ↙️

Jeremy: To close, I asked Julia Sherwin to share her favorite newsletters. Julia is an assistant publisher at GlobalPost Media. She’s also executive director of the GlobalPost in the Classroom, a program that offers free subscriptions to faculty and students at high schools and universities worldwide.

I asked for Julia’s take because I love GlobalPost. It’s great for discovering interesting issues in countries around the world. The editors pick fascinating focal points each day beyond the conflicts, natural disasters, and political battles that dominate much of U.S. international coverage.

15. Tangle

Julia: This free newsletter provides insights into the political forces within America, as well as its international activities. The coverage is consistently honest and nonpartisan. Editor Isaac Saul and his writers focus on one major issue each day, giving readers more than the surface view. Tangle also has an accompanying podcast. The newsletter and podcast feature commentary from both the left and right. A recent issue clarified complex elements of the U.S.-Venezuela oil deal.

16. Global Highlights Newsletter from The Conversation

This is a free, twice-weekly selection of articles written by academics and researchers from around the world. It helps readers understand current geopolitics, scientific news, and historical context.

17. GlobalPost

Julia: Finally, a shameless plug. I work here, but I genuinely haven’t found a news source quite like it: GlobalPost is a nonpartisan daily newsletter devoted entirely to international news: four top stories, plus a fifth dedicated to a scientific discovery.

Recent editions have covered everything from ancient Roman firefighters to scientists recreating the primordial “soup” of the Big Bang to a Western Han dynasty site in China where archaeologists uncovered ancient game boards.

A full subscription is $46 a year with a 14-day free trial. But students and faculty at middle schools, high schools, and colleges can sign up to read it for free.

Now that fall is here, my focus has been fragile.

Noise, notifications, news, and email grab at my attention.

To help cope with distractions, I've stitched together a focus toolkit with apps, sites, and sounds. Some are new, others old. My goal this season is to concentrate for a bit longer when my attention might otherwise drift. I hope this collection will be useful for you too.

Stop email interruptions 📧

Inbox Pause

This simple email add-on temporarily freezes what you see in your inbox. Any new messages will show up as soon as you un-pause.

Price and platforms: Free for basic use. For extra features, like custom scheduling or hearing from select senders during pauses, get the $15/month pro account. Works with Gmail and Outlook online or on the iPhone. An alternative free option: Pause Gmail

Avoid distracting sites 💻

News Feed Eradicator

Get rid of the addictive endless feed on social media sites like Facebook, Twitter, Reddit, YouTube, and LinkedIn. Look instead at whatever accounts you’re actually interested in.

Price and platforms: Free. Chrome only.

Raycast Focus Mode

Block email and distractions during short, focused, work sprints.

Price and platforms: Free. It can automatically block sites for you in Safari, Chrome, and Firefox (and related browsers modeled on WebKit, Chromium, and Firefox).

SelfControl ⏳

Pick a list of sites to block. Set a timer for deep work. While it’s active, you won’t be able to use Facebook, email, or whatever you’ve blacklisted, even if you restart your computer.

Price and platforms: SelfControl is free for Mac. It’s open-source and not fancy.

Alternative: Cold Turkey is a more polished free Windows and Mac alternative for blocking sites. The pro version costs $45 for a lifetime license ($36 for students) for advanced features like blocking applications.

Forest App

Rather than blocking sites or apps, Forest helps you avoid wasting time on your phone by rewarding you for not touching it. Your virtual trees grow until you pick up your phone. The approach seems to resonate: 60 million people have used this app. 🌳

Price and platforms: Free for iOS and Android. A paid subscription unlocks extra features.

Apple Screen Time

Set time limits on apps that tempt you to doomscroll. Count how many notifications your apps send, and see how much screen time you’re logging. The downtime feature is what I use most. It closes my apps at 11pm. I can override that when I need to. But I like that friction nudging me to stop late-night work.

Price and platforms: Free for Macs and iOS devices. Android has a related “Digital Wellbeing” feature. And Windows has focus options. There’s a related Do Not Disturb mode for Mac and iPhone.

Wonder Tools Quick Survey

Help me understand who reads Wonder Tools and what matters to you. It takes about a minute. As a thank you, you’ll get my updated list of 100+ favorite tools in an email within days of submitting it. Your responses are confidential.

Block noise 🔊

Sony Noise Cancelling Headphones

The New York City subway is painfully loud. So I splurged on these over-the-ear WH-1000XM6 headphones. (My previous XM3 pair lasted for seven years until I accidentally bent them.) The battery lasts for several weeks on a single charge.

Price: $460. The XM5 model, also excellent, is $300. Wirecutter’s review (which agrees that Sony’s XM6 model is the best) includes a $100 alternative.

MyNoise

Pick your favorite type of focus sound: a waterfall, a purring cat, white noise, rain, or a dozen others. I like the cafe, where you can adjust the ratio of chatter to kitchen noise. The creator, Stéphane, records real sounds and wrote a manifesto about avoiding AI-generated noise. The newest release: Pigeons of NYC.

Price and platforms: Free, browser-based.

Headspace

This was designed as a meditation app, but I use the focus music without lyrics to block noise around my Times Square office.

Price: $70/year or $10/year for students. Or share six accounts (family, roommates, teammates, etc.) for $100.

A Soft Murmur

Mix a range of sounds to block out city noise or whatever annoys you. Customize and save your own sound mix. Here’s my blend of waves, wind, and white noise.

Price and platforms: Free, browser-based.

Give your body a break 🧍

Wakeout

Take quick exercise breaks with short video loops showing real people doing cardio moves. I like one-minute exercises. The newest version adds little movement games. Body breaks improve my focus.

You can also use Wakeout to pick apps that pause when you’ve been sitting too long. Moving brings back access. (Manoush Zomorodi’s new Body Electric book makes an excellent case for the value of quick movement breaks.)

Price and platforms: The Chrome browser extension is free; a subscription for iPhone, iPad, Mac, and Apple Watch is $70/year or $13/month.

Time Out

Rest your eyes periodically if you work at a screen. I set Time Out to remind me to give my eyes a screen break every 15 minutes. You can choose your own interval. It nudges me to look out the window and stretch. It’s an old app, but it still works.

Price and platforms: Free, optional contributions of $5 to $60. Mac only.

Alternatives: BreakTimer is simple, free, and works on Mac, Windows, and Linux. Restier is a little more polished and also works across platforms; $9 for one device or $15 for two. Lookaway is an elegant Mac option that starts at $19.

Nex Playground

I spend most weekdays standing in front of my computer, so I love how the Nex gets me moving. Its 60+ motion-sensing games are played with your body, not thumbs or controllers. My daughters, wife and I have it linked to our New York City apartment TV and I appreciate how it boosts my energy for evening work. It’s also great for short breaks that reset my focus when I work from home.

Price: $300, plus an optional $89/year subscription for all 60+ games

Hold yourself accountable 🤝

Focusmate

Pair up with an accountability partner online. Pick a time on the site’s calendar when you want to get work done. Choose an interval of 25, 50, or 75 minutes. You’ll be paired with a real person who also wants to stay focused. Log in at the appointed time.

I was originally skeptical about this “body doubling” tactic. I found, though, that an appointment with another human made it feel like a special work interval. It did feel a bit silly to have to meet a random person over Zoom to trick myself into concentrating. But if that’s what works, I’ll do it on occasion.

Price and platforms: No app or download required. Works on any computer or mobile device with a camera and microphone. Free for up to three sessions a week, or $8/month billed annually for unlimited.

Stickk

Pick a goal and create your own commitment contract. You can pledge to donate to a cause you don’t support if you fail to follow through on your resolution.

Price and platforms: Web-based. No cost beyond what you decide to commit.

BeeMinder

Make commitments tied to data you sync. Works with categories like time spent on Facebook or whatever else you choose to sync from Toggl, Fitbit, or other time or health-tracking platforms. Here’s a video explainer.

Price and platforms: Web-based. Free or $8/month for extra features.

Learn new strategies 📚

Tranquility by Tuesday

My favorite book by Laura Vanderkam offers nine ways to make time for what matters. I like her suggestion about carving out a time slot toward the end of each week expressly for finishing things you’ve fallen behind on. I enjoyed talking with her about her latest book, and you can read more of her tips in her Vanderhacks Substack.

Deep Work

Cal Newport is a computer science professor and New Yorker writer who argues that computers and other devices can ruin our focus if we don’t use them thoughtfully. I found it helpful in exploring how to separate technical and menial tasks from work that requires slow, non-linear thinking.

Indistractable

Nir Eyal stuffed his excellent guide to staying focused with useful insights. It’s full of research-backed ideas for combatting internal and external distractions.

What Helps You Focus? Leave a Comment

Today I’m sharing a guest post on how to strengthen your AI skills. It’s by Frank Andrade, an AI instructor who has helped thousands of people on Substack master ChatGPT and Claude with beginner-friendly guides and in-depth tutorials.

Frank: The gap between AI novices and experts is growing.

* One group is saving 5 minutes on emails.

* Others are running systems that work while they sleep.

The good news? You can progress faster than you might think.

The Five Stages:

* Stage 1: AI Beginner

* Stage 2: Prompt Crafter ⬅️ (where many people stall)

* Stage 3: AI Literate

* Stage 4: Workflow Builder

* Stage 5: System Builder

Regardless of which stage you’re at, the resources in each section below will help you sharpen your AI skills.

Stage 1: AI Beginner

This is where everyone starts.

You have a ChatGPT, Gemini, or Claude account. You use it like a fancier Google. You ask one-off questions. Maybe you ask it to help write a quick email or generate a few images. That’s about it.

It’s useful, but it doesn’t feel like a superpower yet. Don’t worry. We’ll get there.

The first move at this stage is picking your tools.

AI tools fall into two categories:

* General-purpose: Handle multiple tasks including text and visuals

* Task-specific: Focus on a specific kind of content or media type

Frank’s Recommended Toolkit

Start Here

Claude, ChatGPT and Gemini

Worth Exploring

Gemini Notebook, Claude Cowork, and Claude Code

Specialized Tools

Gamma (presentations), Google’s Nano Banana Pro (images), ElevenLabs (audio), HeyGen (video), and Napkin (infographics)

The Big 3: Select a Starting Point

For beginners, the differences between ChatGPT, Gemini, and Claude aren’t significant. Still, here are some things to keep in mind:

* ChatGPT: rich feature set, including voice and video modes and image generation

* Gemini: works well with Google Docs, Sheets, Gmail, YouTube, etc.

* Claude: strong at automation and building tools/apps; doesn’t generate photos or videos, though it does assist with design

If you’re a beginner, pick one to focus on. It’s fine to select what your company provides, what’s familiar, or one you’re curious about. Stick with it for a few weeks to see when it saves you time, how well it handles technical tasks, and where it’s most useful.

Frank’s current stack: Claude Cowork, and Claude Code for serious work, Gemini Notebook for learning, and ChatGPT for voice.

Your stack doesn’t have to look like mine. Build your own based on what you actually do.

Here are some of my resources for this exploratory stage:

* The Best AI Tools for 2026

* Your Guide to ChatGPT

* Claude for Beginners: Complete Guide

Stage 2: Prompt Crafter

When it comes to AI chatbots, how you ask is as important as what you ask.

At this stage, get to know this basic prompt structure:

* Instruction: what you want

* Context: background the AI needs to know

* Constraints: length, tone, format, things to avoid

* Example: when possible, provide an example of what “good” looks like

For more detail, refer to this robust prompt formula shared by Anthropic, which makes Claude:

You’ll rarely need to use all the elements of the formula, but it’s good to know they exist. Think of them as a menu to pick from.

At this stage, you should also know a few prompt-improvement tricks. For example, when you finally land on a great answer after a long back-and-forth, ask the AI to write the prompt that would have gotten you there on the first try.

Here are some resources for this stage:

* Prompt Formula

* Prompt Principles

Who Needs to Go Beyond Stage 2?

Stage 2 was enough in 2023.

In 2026, AI has evolved and can run multiple tasks at once on its own. There’s nothing wrong with being in stage 1 or 2 if you’re a casual user who proofreads emails and generates images once in a while

But if you want to master AI, you need more.

That’s what we’ll cover in the next stages:

* Stage 3: Develop AI literacy. Use it as a thinking partner.

* Stage 4: Build AI workflows for the work you do repeatedly.

* Stage 5: Build AI systems that run while you sleep.

Stages 3, 4, and 5 are for professionals, builders, and business leaders who want to turn AI into a competitive advantage.

Stage 3: AI Literate

Understanding how AI actually works changes how you use it.

People with AI fluency know when to trust AI outputs, when to push back, and how to frame problems to get more useful results. That’s what separates those who use AI as a novelty from those who deploy it for its practical advantages.

People at this level know these AI concepts:

* Hallucinations: AI can confidently fabricate facts, stats, and citations. Always verify outputs when accuracy matters.

* Context Window: AI assistants can remember a limited amount per conversation. Once that limit is exceeded, your AI forgets earlier context.

* AI Sycophancy: AI models are trained to be helpful, sometimes to a fault. They may validate your perspective even when you’re wrong. They rarely challenge assumptions unless prompted.

* Knowledge Cutoff Dates: Models generally have training cutoffs. That means they may not know about recent events. If an AI assistant has access to web search, it can gather new info.

* Data Bias: AI inherits biases from training data. Be cautious when using AI for decisions about sensitive topics.

* Privacy & Safety Basics: Know the data policies for your AI tool and your organization. Read about how to use private AI tools for free, and how to set up a private AI toolkit.

Having AI literacy means knowing how to manage AI limitations.

Example: Let’s say you’re a leader who wants to combat AI sycophancy to make better decisions. Create anti-sycophancy instructions that nudge an AI assistant to disagree with you constructively.

At this stage, move from “AI thinks for me” to “AI helps me think better.”

That means using AI as a sparring partner. Here are some ways to do that:

Ask AI to generate different solutions and grade them

“Generate three solutions. Score them from 1 to 10 and justify the score.”

Use AI to critique responses, opinions, plans, etc.

“Be my adversarial friend. Argue the strongest case against Option A. List five reasons why it might fail and the early warning signs. Suggest five ways to reduce those risks.”

Generate questions to refine outputs

“Before drafting anything, ask the five questions that would most alter the outcome of this memo: [1-sentence purpose].”

Resources for this stage:

* How to use AI as a thinking partner

* Before your next big decision, build this Claude skill

* Books to increase your AI literacy

* How to build your AI Mentor

Stage 4: Workflow Builder

The trick at this stage is designing your own workflows, not using more tools.

A workflow is a multi-step process where AI plays a role at each step. You might still drive it by clicking, uploading, and reviewing. But you don’t start from scratch every time.

Here’s a workflow I built:

Learn a foreign language with AI

* Step 1: I answer questions about my learning preferences, challenges, and goals

* Step 2: AI generates a “language DNA profile”

* Step 3: I record myself speaking the language for five to 10 minutes → upload the transcript + my DNA profile → AI gives feedback tailored to me

This is a workflow rather than a full automation because I still trigger each step. I generate a profile. I upload the inputs. I hit go.

Here’s how to build your own AI workflow:

* Pick one task you do repeatedly and turn it into a 3-step workflow

* Pick one or two tools to help you optimize this workflow

* Write a prompt for each step. If possible, add examples of what “good” looks like.

* Test it with a real example and iterate until the output is what you need

* Set up a Project (in ChatGPT or Claude) to keep your context, instructions, and reference files in one place

Resources for this stage:

* Claude Cowork for beginners

* Claude in Chrome

* Claude Skills: part 1, part 2

* Before you use Cowork, create this file

For most professionals, this stage is more than enough. But if you want to multiply your output without working more hours, there’s one more level.

Stage 5: AI System Builder

Stage 4 was about workflows you run. Stage 5 is about systems that run themselves.

There’s a mindset shift here.

You stop asking, “How do I do this faster?” Instead, you frame the question as, “How do I build something that does this for me, even when I’m sleeping?”

Here’s a system I recently built:

The problem: I publish daily Substack notes. Many of my notes are inspired by viral content I find on Instagram, YouTube, and X. The old process took hours every day: saving links, watching videos, downloading images, writing hooks, etc.

The system I built (simplified):

* Collection: My team and I save viral content to a shared group chat throughout the day

* Trigger: At 3 a.m., an automation kicks in (I’m sleeping)

* Processing: Claude reads the group chat, checks what’s new for today, then downloads everything (text, images, videos)

* Generation: Each piece runs through my Substack notes generator (a separate workflow that uses my brand voice and note formats)

* Output: When I wake up, I open my “Today” folder. Inside are 3 subfolders: YouTube, X, and Instagram. Each has media content + 5 draft notes ready to edit and post.

I pick one draft, edit it, and post it. What used to take two to three hours now takes minutes.

To build AI systems, you need tools that go beyond chatbots:

* Claude Cowork: My favorite for delegating things to Claude without being technical. It runs in a sandboxed environment for safety, so you may run into limitations.

* Claude Code: A more advanced version of Cowork. I use it whenever Cowork can’t build something for me. You don’t need to be a coder. You describe what you want, and it builds it. Caveat: it can feel scary at first.

* n8n: Popular no-code tool for AI agents and multi-step systems. I don’t use it, but many builders do.

Resources for this stage:

* How to set up Claude Cowork

* How and why to set up scheduled tasks

* Google Doc list of AI guides

Two Final Tips

* Don’t skip stages. AI literacy and prompting may feel boring compared with building your own app, but they make every stage above them work better.

* You don’t need to be at Stage 5 to get serious value. Many professionals get a 2x improvement just from reaching Stage 3.

Pick one stage above where you are right now and focus on it for the next few weeks. That’s how you’ll go from AI beginner to pro by the end of 2026.

Thanks to Frank Andrade for this guest post.

Google Docs turned 20 this year, so I’m sharing 20 of my favorite GDocs features you might find useful. What are your favorites?✨

1. Type with my voice 🎙️

Tools > Voice typing

When I’m tired of typing, I dictate. I like voice typing with Google Docs to add sentences to a blank page as I think out loud. Here’s a sample of my dictated text. Read it aloud to test your voice typing. The transcription isn’t perfect, but it’s free.

2. Match a prior doc’s format 📋

File > New > Help me create > Match doc format

I can base any new doc on a prior design, like my pedagogy resources handout. This gives me a quick way to create new styled drafts. Requires Gemini to be turned on.

3. Add extensions 🧩

Extensions > Add-ons

Get apps for GDocs. I like Beep for attaching voice notes to docs. Word Cloud Generator is nice too. Here’s an example, drawn from this post. Docs to Slides by Alice Keeler is useful for converting a doc into a presentation. The Free icons extension from icons8 is useful for easily adding little visuals to a doc.

4. Add a quick link to any text 🔗

Type Command+K with any word or phrase selected

Google Docs is the most efficient tool for adding links to text. Select a word and press Command+K to choose from several relevant links without leaving the doc. It helps me avoid opening a separate tab to hunt down links. Here’s a gif showing this.

5. Quickly create a new doc ⚡

Type doc.new into any browser to quickly create a document.

This shortcut lets you jump into a new document from any browser window. It works with other Google services too: slide.new, sheet.new, form.new, site.new, cal.new, meet.new, and keep.new. It also works for notion.new, canva.new, substack.new, and playlist.new (Spotify). More examples.

6. Divide a doc into sections 🗂️

Insert > Tab

Instead of creating 20 files for a project, make a single doc your headquarters. Each topic can have its own tab. Or each team can. Share everything with one link instead of maintaining a dozen separate docs. See my tips for tabs then add your own idea in a comment. (View a published GDoc version to see the difference between shared docs and published ones).

7. Add a table of contents 🧭

Insert > Table of contents

For long documents, create a table of contents (TOC) so people can quickly find what they need. Choose the black text option for a cleaner look, if you’re printing.Add headings within the doc (Format > Paragraph styles) to ensure they appear in the TOC. Here’s step-by-step help on this if you need it.

8. Keep track of changes 🕰️

File > Version history

Version history makes it easy to see what you’ve changed, when. Or look at what collaborators have edited. See what’s new, who made an edit, and when.

9. Copy a doc 📑

File > Make a copy

Duplicate something to make a different version. Simple, easy, and fast. Sometimes I use this for version control instead of the built-in version history.

10. Download a PDF — or other formats ⬇️

File > Download > PDF Document

Sometimes I need to share a PDF so anyone can easily read my doc. Nothing fancy, but it’s been useful hundreds of times.

11. Create typing shortcuts ⌨️

Tools > preferences, then select Substitutions on the top right.

Use shorthand with GDocs for words or phrases you frequently type. List them in your preferences. For each one, pick a simple key combination of letters. From then on, any time you type those letters, they’ll expand into your desired phrase. It’s useful for your email or mailing address, or a word you often misspell.

12. Try new templates 🎨

File > New > From a Template

Start from a design instead of a blank page. Google now has more than 100 templates, including 60 in the template gallery and 40 when you choose the “from a template option” to start a new doc. The new project roadmap and onboarding templates are well-designed. The resume, letter, and proposal templates also make your words look good. Some of the other templates are a bit visually bland.

13. Design docs for the web 🖥️

Format > Switch to Pageless

Many of the docs we create never need to be printed. So GDocs now offers a pageless format for docs you’ll use on screen. It lets you include wider images and eliminates artificial page breaks. See a gif of Pageless view. Here are a few more points about this format.

14. Listen to your words 🎧

Insert > Audio Buttons

When I hear my writing read aloud, the clunky bits jump out. That helps with editing. When an AI voice reads my writing, I can look away and devote my full attention to listening. This feature lets you choose from seven synthetics voices. They don’t sound like robots. This feature requires an AI subscription or an eligible Google Workspace plan.

15. Get proofreading help 🔍

Tools > Proofread

Check for spelling or grammar errors. Get suggestions for where you might break up overly long sentences or avoid passive verbs. You accept or reject changes one by one. I like getting to decide which fixes make sense. It’s like an augmented spellcheck that requires AI settings to be turned on. See it in action on a prior draft of this post.

16. Translate your doc instantly 🌍

Tools > Translate document

Share your doc in another language. GDocs keeps your original and makes a translated copy. It’s not human quality, but it’s enough for the gist.

17. Use markdown for formatting #️⃣

Enable it under Tools > Preferences

Easily add headings, bullets, and other formatting from the keyboard with simple symbols. Use *ital* for italics or **bold** to make something bold. You can also paste markdown text from other apps with Edit > Paste from Markdown

18. See who’s viewing your doc 📊

Tools > Activity Dashboard

A dashboard you may not have noticed shows who else in your organization has viewed a doc and when. You’ll also see a chart showing when comments have been added. It requires Google Workspace, and it’s not available for solo free accounts. Adjust privacy settings to keep your activity secret.

19. Insert interactive elements 🧱

Insert > Building Blocks

Include an AI summary of your document, a decision log, a team directory, a content tracker, or other templated, editable text blocks. Or insert a linked doc that updates automatically when you update the original file.

20. Link to people, events and docs with Smart Chips 🏷️

Insert > Smart chips

Smart chips let you paste a live link into docs with a preview. Type @ and the name of a person, place, or calendar event to insert a preview that pops up when someone scrolls over the item. See Google’s help explanation.

Bonus tip: Add more fonts 🔠

Fonts > More fonts

Georgia, Raleway, Proxima Nova and Oswald look good. And they’re easy to read. But experiment with other new fonts. Use WhatTheFont to identify other fonts you see and like online.

5 ways GDocs disrupted word processing 🚀

Free. Make and store thousands of documents at no cost, with no ads.

Auto-Save. Write without fear of losing files. Work is auto-saved constantly. I remember the frustration of losing docs when Microsoft’s old Word crashed.

Accessible. Get access to your documents on any device. No need to carry disks around or have a specific device to access important files.

Collaboration. Share docs with others, or publish them. I’ve used docs to liveblog, to share examples publicly. Or work privately.

Simplicity. Just start writing. No complicated menus. It just works reliably.

See more Wonder Tools posts about Google Docs 🪎

Good alternatives to Google Docs 🔄

* Kraa is a slick text editor I like. Create simple, polished pages like this gallery, library, or archaeology article. It has new sharing features. The iOS app is coming soon.

* iA Writer offers a simple, minimalist writing view.

* Versey is a promising new option I’m testing, with AI to help with editing. Textjam and Reproof are others I’m trying, though not yet recommending.

* Superhuman Docs, formerly called Coda, is underrated. It’s an alternative to Notion that lets you incorporate AI in your workspace and connect documents to your calendar, CRM, email, and Slack.

* Craft remains one of my favorite tools for creating visual handouts.

* Scrivener helps keep long writing projects organized.

What’s your favorite Google Docs feature? Leave a comment 👇

I’m excited to be starting a new semester this week, like millions of other teachers. As a resource for my fellow educators, I’m updating a piece I wrote for The 74, the nonprofit education news site.

The average K-12 teacher works 49 hours a week. About a quarter of that time is uncompensated. In higher ed, adjuncts make up about 40% of the faculty workforce. At many institutions, time spent on course prep and administrative tasks is unpaid. Most teachers I know didn’t become educators to spend evenings generating quiz questions, rewriting instructions, or filling out administrative paperwork.

AI assistants like Claude, ChatGPT and Gemini won’t change these realities. But when you’re overwhelmed, they can help streamline tedious tasks. They can free up energy for what only a human teacher can do. When used thoughtfully, these tools can actually push us to be more creative. They can help us overcome teaching ruts, nudging us to revitalize how we show up in the classroom.

A 60-second guide to prompting

The first step to making the most of AI is understanding how to use prompts. A prompt is a natural-language instruction to an AI assistant. It doesn’t have to include technical or formal language. You don’t even have to use full sentences.

Prompts work with any AI assistant. Use free private AI chatbots, like Proton’s Lumo or Duck AI. Or download AI apps that run on your laptop without touching the Internet, like Jan, which I tested and recommend. Claude, Gemini, and ChatGPT also work well. Whatever you have access to will work.

As the teacher, you guide an AI assistant with relevant context. Prompts work best when they include specifics. Generic prompts yield generic responses.

It helps to iterate on AI output with follow-up prompts. Ask for more specificity or detail. Adapt the response for your students. Don’t use it as is. Part of retaining your agency in the process is making sure you build on whatever outputs an assistant generates. You’re the director. It’s much like adopting an open educational resource. The advantage, though, is that this material will be more tailored to your students and teaching approach.

Knowing how to use prompts effectively can mean the difference between AI that’s actually helpful and AI that’s gimmicky. The prompts below offer a creative boost. Each illustrates a practical way to use AI in support of thoughtful, pedagogically sound teaching. You don’t need any special technical skills. You don’t need paid AI subscriptions. Customize them to suit your subject matter and your approach to teaching.

Try my new free Teaching Prompt Assistant. Give it your goal and it’ll guide you quickly to a draft prompt.

Start with a project

If you want to use prompts more efficiently, first create a project in Claude or ChatGPT, or a Gemini Notebook. Think of this as a folder where you provide context about your class that an AI assistant can reference when you ask for support. You can upload past materials, syllabi, lesson plans, curriculum guidelines, Common Core State Standards, or whatever else is relevant for your teaching.

You can also add detailed instructions to the project explaining how you’d like the AI to assist you. You’re teaching it your preferences. Once you set up a project, you won’t have to repeatedly type in the same context.

The Prompt Collection

1. The Bell Ringer

Start class with a spark

The first five minutes of class set the tone for everything that follows. A short, well-designed opening activity can draw students in. Engaging openers are especially valuable on Mondays, after vacations, or when you’re pivoting to a new topic. The challenge is coming up with fresh ones regularly.

Goal: Generate five quick options for activities you can use at the start of a class session, adapted for your subject and your students.

Prompt: “I teach [subject x] to students in [grade level x]. We’re studying [specific topic xyz]. Generate five activities I can adapt to start a [xx] minute class. Each should take no more than [x] minutes, require no materials, and either activate prior knowledge or help students reflect on what they’ve just learned. Include one that’s discussion-based, one that’s written and one that’s a game or visual/creative task. [Or adapt these examples to reflect your subject matter. For example, one of the options could be a logic puzzle or an artistic challenge].”

Tip: Be as detailed as possible about your preferences. Include a sentence about your teaching style and context about your students. No need to make it formal.

See an example of a Bell Ringer Prompt

2. The Real-World Hook

Answer “Why does this matter?” before students even ask

When you’re overwhelmed by administrative meetings, multiple preps, and paperwork, it can be hard to give extra attention to helping students relate to a new unit. This prompt helps you brainstorm connections to contemporary music, art, film, TV, cultural trends or other subjects of interest to students.

Goal: Generate five ways to show your students how the topic you’re teaching is relevant to their lives, each with a two-sentence hook you can use to open discussion.

Prompt: “I’m about to begin a unit on [x topic] with [grade level x] students. [Provide a sentence of additional context and a few additional details about your students’ interests]. Generate five ways to connect this material to something students are likely to relate to. This can include sports, the arts, social media trends, pop culture, music or other contemporary issues. For each connection, suggest a two-sentence hook I can adapt to help jumpstart a class discussion.”

See an example of a Real-World Hook Prompt

3. The Bad Example Generator

Turn common mistakes into learning opportunities

Showing students examples of mistakes can help them avoid those pitfalls. But you can’t embarrass students by showing examples of their weakest work. Fortunately, AI assistants are excellent example generators. They can come up with nearly any kind of error you specify. No need to spend hours creating intentionally bad work.

Adapt this prompt to include any kind of error you want your students to avoid. These can include experimental design mishaps in science or mangled math formulas. If you’re teaching essay writing, showcase logical fallacies or ad hominem arguments.

Here’s an example of a table of common writing traps I generated.

Goal: Produce five realistic examples of a specific error type, unlabeled, so students can identify, discuss and learn from the flaws.

Prompt: “I’m teaching [x subject/topic] to [grade level x] students. [Provide an additional sentence of specific context about your class, the learning goals you’re focusing on, and/or the lesson you’re preparing.] Generate five examples of paragraphs with [ad hominem arguments / circular reasoning / weak thesis statements / misleading use of statistics / or pick any other weakness] related to [x topic]. Make sure each example is realistic. These should be the kinds of errors students at this grade level might actually make. Don’t label what’s wrong. I’ll use these for a class activity where students identify and explain the flaws themselves.”

Tip: You can also task the AI with annotating or explaining these errors to help you walk students methodically through these common flaws.

* See how a specific teacher might use the Bad Example Generator

* Try my free “Wrong On Purpose” tool to generate examples of what to avoid that you can tailor for your class. (Requires a free Claude account)

4. The Scaffolding Prompt

Make instructions clear for every student

Complex instructions often trip up students. Simplifying language can help, along with breaking guidance into smaller steps. This prompt helps you clarify instructions for an existing assignment, handout, or any other activity. It’s particularly useful if you have students with learning differences or if your class has a wide range of readiness levels.

Goal: Reframe a handout or assignment so it’s clearer and more accessible, especially for students who need extra support.

Prompt: “Here is a [handout / assignment / resource] I give students: [paste or upload it]. Help me reframe this for students who face [specific challenges or context]. I particularly want this to be more accessible for students who need extra support. Break the instructions into smaller, numbered steps. Replace any abstract language with concrete directions. Point out any parts I should clarify. Suggest a brief example for each major step and any illustrations or images that might help me make this more visually engaging. Maintain the academic expectations I have for the work.”

See an example of a Scaffolding Prompt

5. The Review Game Generator

Develop review questions efficiently

Coming up with a long list of review questions can take hours. And designing plausible wrong answers can be exhausting. An AI assistant can help, quickly turning existing handouts, lesson plans, or fact sheets into engaging questions, customized for your subject and student level. Tip: Add questions you’ve used in the past to the prompt as a model for the AI assistant to learn from.

Goal: Generate 15 multiple-choice review questions, tiered by difficulty, formatted for whatever learning game you prefer.

Prompt: “I’m finishing a unit on [x topic] with my [grade level x] students. For an upcoming review session, I’m preparing material to help students practice [a particular skill or area of knowledge]. Generate 15 questions based on the following key concepts: [list concepts or paste notes or upload a handout]. For the multiple-choice ones, include a correct answer and three plausible wrong answers. Vary the difficulty: five easy, five medium, five challenging. Flag the correct answer for each. Also suggest some true/false, fill-in-the-blank, and open-ended questions for variety.”

See an example of a Review Game Prompt

6. The Fresh Angle Search

Bring new life to familiar content

Some topics get stale, especially when you’ve taught them the same way for years. To liven up an old lesson, it can be helpful to gather new sources, examples, statistics, case studies or unexpected angles.

Use Perplexity, a free, AI-powered search engine that provides citations alongside its results. Its links ensure you have an evidence trail to verify its responses and explore the original sources. Digging into Perplexity’s concise search summary is more efficient than sorting through hundreds of Google links.

Goal: Find five recent or unexpected real-world examples of a concept you’re teaching, including perspectives from outside the U.S. and connections to students’ current interests.

Prompt: “I teach [x topic] to [grade level x] students. [Provide additional context here about the topic or learning outcomes you’re focused on]. I’m looking for interesting material [or whatever other description you prefer] to make this subject more engaging for students. [Include any additional context about your students’ interests]. Find me several recent, unexpected or counterintuitive real-world examples of [x concept] that might surprise or intrigue students. Include real-world details to help add nuance for students who think they already understand the concept. And suggest multiple new analogies I can use for students who don’t yet understand this concept. Include international examples, and at least one that has an element of humor.”

See an example of a Fresh Angle Search

7. The Skeptical Student Prompt

Prepare for the hardest questions before class starts

You never know what odd questions might arise when you teach a new topic. AI assistants can help by generating all sorts of potential questions. That prep can help you avoid unpleasant surprises in class, so you’re ready for nearly anything students might toss at you.

Goal: Generate 10 challenging questions a skeptical student might ask me about this lesson.

Prompt: “Here is a [lesson plan / reading / concept] I’m teaching: [paste or upload material, mentioning the grade level and any other relevant context]. Give me a list of potential student questions about the relevance of this new topic and about real-world applications. Also note any doubts students might have. If these students [at grade level x] are skeptical that this material is relevant, what might they wonder, and what aspects in particular might they question? Generate 10 challenging questions curious students might ask. Include ones that challenge the relevance of the topic, the reliability of my sources, and the assumptions behind my explanations.”

See an example of a Skeptical Student Prompt

8. The Blind Spot Audit

Find your own blind spots before students do

During a typical week, we don’t always have time to trade peer feedback on lesson plans or syllabi. But we can still benefit from getting input on our materials. AI assistants can critically evaluate your materials for clarity, accessibility, inclusivity, or blind spots. You always have the option of ignoring the observations. I usually like at least a couple of the proposed adjustments.

Goal: Identify specific places in my lesson plan or syllabus where I might have an unconscious bias, where my instructions may be unclear, or where my examples may not reflect the diversity of my students. Point out any unnecessary jargon and highlight assessment criteria that might be confusing.

Prompt: “Here is my [lesson plan / syllabus / unit overview]: [paste or upload document]. Take the perspective of a critic with expertise in inclusive pedagogy and student-centered design. Identify parts of my plan that may not work for students with vision, hearing, or mobility impairments. Also point out places where an unconscious bias might be influencing the way I’m presenting this topic. Point out places where examples or explanations I’ve included might not make sense to my diverse students. Show me places where my assessment criteria could be clearer. Note any other sections of the material that might not be inclusive, accessible or relatable for students. Be direct. Include the location of each issue so I can explore potential fixes. I want specific critique, not general praise. Explain each observation in detail.”

See an example of a Blind Spot Audit

9. The Differentiation Prompt

Adapt an assignment for distinct levels

In many classrooms, students arrive at varying levels of readiness. But consistently creating multiple versions of the same material can turn 40-hour weeks into 49-hour marathons. An AI assistant’s suggested adaptations can help.

Tip: make sure your differentiated materials remain anchored in your own ideas and teaching goals. There’s a risk of cognitive offloading, where you start letting the AI make decisions for you. Avoid that by treating any response you get as a preliminary thought that you shape yourself.

Goal: Produce alternative versions of an existing assignment: one with additional scaffolding, and one with stretch challenges for advanced students.

Prompt: “Here is an [assignment / assessment] I give students: [paste or upload material]. Generate two versions of this: one for students who need additional scaffolding and more explicit guidance, and one that adds stretch challenges for advanced students. Preserve the core learning objectives. Summarize the suggested changes and explain their rationale, so I can decide how to adapt these alternatives for my students.”

See an example of a Differentiation Prompt

10. The Rubric Builder

Help students understand how you’ll assess them

A well-designed rubric does two things: it clarifies your expectations before students start working, and it gives them a roadmap for revising. Developing rubrics from scratch is tedious. It requires formatting small batches of text into boxes in complex tables. This prompt generates a structured first draft in table format. You can then refine it before sharing it with students. To start, specify the elements of the student work you’ll be evaluating, and describe your criteria.

You don’t have to use full sentences or formal language. Just describe what constitutes excellence for this assignment, what satisfactory work looks like, and what evidence signals to you that a student may need more practice. Crafting these rubrics with AI assistance is an iterative process. Revise initial outputs by adding your own details and refinements.

Goal: Generate a rubric written in clear, concrete language that helps students understand how they’re going to be evaluated.

Prompt: “I’m assigning [assignment description] to [grade level x] students. [Here’s a bit of relevant context]. Generate a rubric with three performance levels: Excellent, Proficient, and Developing. (Or Superb, Good, and Needs Improvement). Include five criteria relevant to this assignment: [list criteria, e.g., use of evidence, originality, thoughtfulness, structure, and mechanics]. For each criterion and each level, write two specific sentences describing what that performance actually looks like. Avoid vague language like ‘good use of sources.’ Put this rubric into a table, then wait for my edits.”

See an example of a Rubric Builder

11. The Case Study Collaborator

Generate fictional scenarios to spice up discussions

Case studies help spark lively discussions. They’re useful whether you’re introducing students to ethical questions or trying to help students relate to a historical situation. They can also bring a business decision or scientific discovery to life. Creating cases from scratch can be grueling. So this prompt helps you build fictional but realistic scenarios customized to your subject matter and student context.

Goal: Create a fictional case study to illustrate a tension relevant to your subject, set in a context students can relate to, ending with three discussion questions.

Prompt: “I teach [x subject] to [grade level x] students. [Provide an additional sentence of context or specifics to ensure the case studies are relevant and useful.] We’re exploring [x concept or issue. Include as much detail as possible about what and how you’re approaching the topic and your learning goals]. Create a fictional but realistic case study I can use in class next week that is timely and involves [a relevant character, institution, or situation] that illustrates the tension between [value A] and [value B]. Set it in [context relevant to your students: a school, a local community, a specific industry]. Make sure the scenario is complex enough that reasonable people could disagree about what response makes the most sense. End with three discussion questions that I can adapt to push students to apply the concepts we’ve been studying.”

See an example of a Case Study Collaborator

A final thought

AI assistants have arrived at a time when teachers need support to do their best work. In a national survey by the RAND Corporation, just 24% of teachers reported being satisfied with their total weekly hours worked, and 66% said their base salary was inadequate. AI tools won’t make up for unfair compensation. But they can help us strengthen how we serve our students while we make time for the rest of our lives.

Share private feedback on Wonder Tools or leave a public comment below. ⬇️

I’ve always admired the way bestselling author A.J. Jacobs turns his life into a laboratory for testing quirky ideas. He’s written books about following every biblical law for a year, reading each entry in the encyclopedia, and thanking a thousand people responsible for his morning coffee. I consider it immersion journalism. He calls himself a human guinea pig.

So I was delighted to meet A.J. at a recent Substack event. Afterwards we spent an hour talking live on Substack about two dozen of the odd and creative tools he uses and trading ideas about our experiments. Watch the recording above, including some surprising confessions, and see a summary of the tools and links mentioned below.

Add surprise to your day

Algorithms narrow what we see and filter outliers. So A.J. seeks out serendipity.

* Wiki Roulette serves up random Wikipedia entries, while Window Swap lets him peer out of windows all over the world.

* Ground News A.J. uses this app to see how outlets across the political spectrum cover the same story. Its Blindspot feature surfaces stories covered mostly by one side. I mentioned a related newsletter, The Flip Side, which picks a daily topic and spotlights commentary from the left and right.

* Seek out surprises A.J. asked Claude for 10 articles he would probably find boring, annoying, or offensive. It surfaced one gem, about ancient Egyptians buried with golden tongues so they could speak in the afterlife.

* Try it yourself Here’s my own anti filter-bubble prompt, and the 5 odd links ChatGPT gave me in my first experiment.

* Serendipitous Reddit For stumbling onto curiosities, I’ll type a keyword into the Reddit search box. During my live chat with A.J. I found r/Whatisit, where people post photos of unidentifiable objects. The crowd figures out what they are. And r/MadeMeSmile, which is heartwarming. Try the free Random Reddit Stumbler Chrome extension to discover new Reddit communities. Caveat: You might waste time procrasti-surfing in rabbit holes.

* A.J.’s NYTimes archive trick Search the Times all the way back to 1851 for a word of your choice, then read early mentions. Searching for “dogs” led A.J. to a disturbing 1896 editorial titled “All Dogs Deserve Death” (screenshot), which argued that dogs spread disease. “It was proof that clickbait is not a totally new phenomenon,” he says. A.J.’s caveat: the archive surfaces ugly history. Searching “cocaine” turned up overtly racist reporting. Accessing the archive requires a subscription.

* Read A.J.’s take on injecting randomness into your life

Play with words

* Parseword The creator of Wordle, Josh Wardle, made this tricky new word game. A.J. describes it as an on-ramp to British cryptic crosswords, which blend wordplay with anagrams and obscure puns. “They’re infuriating,” he says, “but at the same time, very addictive.” I find this one fun but hard.

* Raddle Try this word ladder with a twist. The clues are are out of order. A.J. says he enjoys it because you can finish in two minutes. I appreciate the hints so I don’t get stuck.

* OneLook “An amazing search engine for words,” A.J. says. Type a word and get its history, related terms, definitions from numerous dictionaries, or quotes, phrases, and lyrics that use it. Or use wildcards to find words that start or end with a group of letters. OneLook scans 17 million entries in 805 dictionaries to answer queries. They also designed an amusing new word game called Cadgy.

* Anagram sites. The Word Finder and other multi-word anagram tools like Anagram Solver handle phrases, not just single words. Scrabble Solver helps you find words with your tiles.

* Droodles This playful format for minimalist drawings centers on absurd captions, as in these examples. Play by guessing the captions, or make up your own.

Wake up your senses

* The Sommelier Wine Aroma Kit by Aromaster A.J. bought is a training kit for aspiring oenophiles. It has 88 tiny bottles of individual scents, including Rose and Lemon. Horse sweat, the set’s last bottle, isn’t something you want in a wine. The kit is $400 on Amazon, but you can make a simpler one for $30. A.J. tries to identify scents for three minutes each morning to strengthen his nose for food. Smell is our least trained sense, he says.

* Use your own spice rack When my daughters were little, we’d play a guessing game, taking turns holding a spice bottle beneath our noses with our eyes closed. It entertained us in the kitchen and cost nothing.

* Vision-distorting glasses A.J. ordered 10 pairs that alter how you see. One simulates a bee’s vision. Another tries to represent macular degeneration. Some are prisms that flip the world upside down. He started this exploration after hearing that yellow-tinted glasses brighten your mood. The tint did little for him. But it made a point, he says. “What we see is a very narrow spectrum of reality.”

Watch movies better

* Audio description Most streaming apps have an accessibility feature that lets you hear a narrator describe what’s happening on screen. It’s designed for blind and low-vision viewers. A.J. isn’t vision impaired, but uses it anyway. “It’s educational,” he says. “I learn a lot from the voiceover that I didn’t know before.” Watching an Agatha Christie film, he discovered what a cloche is. And a trilby. The narration also alerted him to a novel detail: the O in the Focus Features logo is deliberately out of focus. A.J. says he admires the concise writing required to fit every word between the dialogue.

* Closed captions A simpler feature we both use. A.J. turns them on for song titles and for accents. “You’re watching Derry Girls and you have no idea what people are saying.” I started relying on captions for The Wire.

* Playback speed A.J. watches films at 1.5x or 2x speed. “I see twice as many movies,” he says. “I admit, I may get 80% as much out of them.” He knows filmmakers hate it.

* Netflix offers 1.5x, but not while casting or on the ad-supported web player

* Apple TV and Prime go to 2x

* Chrome extensions like Video Speed Controller give you finer control

* Slow motion A.J. also watches at 0.5x speed sometimes to study scene design. Dense shows like Veep need to be slowed down, he says, not sped up.

* WhenJumpScare A.J. appreciates psychological horror, but he hates jump scares. This free site tells you exactly when surprises are coming so you can look away. “I love a horror movie,” he says, “and I’m not going to watch it if I’m going to be jumping in my seat the whole time.”

* RunPee (iPhone/Android) This free app (screenshot) tells you the ideal minute to run to the bathroom during a long movie, and sums up what you missed. A.J. used it for Christopher Nolan’s nearly three-hour Odyssey.

Stretch your brain

reMarkable tablet We both own one. I use mine to sync, back up, and organize my handwritten notes. A.J. never connects his to the internet. Every morning he spends ten minutes brainstorming with it by hand.

Sometimes he flips open a magazine for an improvised prompt. He saw a snowman picture recently and started riffing: “What if it’s a snow woman? What if the pipe is a vape? What if the coal eyes are solar panels?”

“99% of these ideas are terrible,” he says. But he doesn’t mind. “If you believe the brain is a muscle, and I do believe there’s something to that metaphor, then this is like going to the gym for me.”

Add color to your space

I shared with A.J. three of the most colorful objects in my office. I have no affiliation with any of these companies. I’m just sharing what’s on my desk.

CMY Cubes A small glass cube reflects light next to my laptop. Each face has a different color. Look through it at an angle and the light refracts into new colors. Designed in Australia, the smallest cubes cost about $23. No batteries, no app. I found mine at the Toy Fair, the annual trade show at NYC’s Javits Center where thousands of toymakers show new wares.

Merge Cube A foam cube that supplements augmented reality apps. When you use a compatible app, each of the cube’s faces renders a distinct three dimensional image on your computer or phone screen. I confess, though, that sometimes I just use it as a stress ball.

T2 double-walled glass tea flask Some teas smell as good as they taste, and some have a lovely tint. I can see, smell, and savor tea with this clear flask I got as a gift. I do wonder, though, if it’ll shatter if I accidentally knock it off my desk someday.

Think with games

Brainspin I use dozens of games in my teaching, including those in my Pinterest creativity card game collection. Brainspin is the simplest. It’s a deck of two-dimensional pictograms I use as a brainstorming warm-up in the classes I teach. $25 for a set of two decks, designed by Frankie Abralind, who is now on Substack.

Bonus links for more of A.J.’s quirky takes on life

* Read A.J.’s newsletter, Experimental Living for more on his adventures.

* Watch his five TED talks for more on his unique life experiments

* Listen to his Puzzler podcast

* Check out his books, which are consistently quirky and funny

I’m looking forward to the book A.J.’s working on next, about misinformation. He’s fact-checking his own life. “How do I know the world is round?” he asks. “How do I know my wife loves me?”

What experiment are you trying these days? Leave a comment 👇

Thanks to Len Netti, Surya, Gary Rudoren, and many others for tuning into my live conversation!

I’ve changed how I use Claude and ChatGPT lately. They’ve become my digital dashboards, linked to many of the tools I rely on.

I can ask Claude to add to my calendar, query my meeting notes, update me on my email, or find a passage I highlighted in my digital notebook.

Claude Connectors and ChatGPT plugins connect to hundreds of services. These include Superhuman Mail for email, Google Calendar, Granola for meeting notes, and Readwise for my online highlights.

Read on for how and why to link your favorite tools to your AI assistant, and examples of connections and queries I’ve found useful so far.

Bonus: I made this new online guide for you based on this post as an experiment with ChatGPT’s new Sites feature. I also made a tipsheet with Claude artifacts to help you get started.

Why Connecting Tools to Claude and ChatGPT Is So Useful

Claude and ChatGPT know the context for my work because I’ve set up Projects for my primary work areas. Each has detailed instructions and reference documents. And the AI has a memory of the work I do, my style, my preferences, and my objectives. So I can ask my AI assistant to:

* Plan: Add four prep sessions to open morning slots on my calendar next week for the classes I’m teaching this fall. Include in each event description relevant excerpts from my meeting summary and reference the recent planning notes I dictated.

* Research: Gather recent links I’ve saved to Raindrop, my bookmarking tool, that might be relevant to my team’s research. Then create a new reminder with those links and a summary of my recent related notes.

These multiple-part commands require context. They won’t work in Google Calendar, Raindrop, or Granola directly. That’s why it’s so helpful to have Claude or ChatGPT as the command center.

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MCP is the New USB 🔗

These connectors have a technical name: MCP, or Model Context Protocol. But just as you don’t need to think about USB details when you plug in a printer, or http specifications when you use the Web, you can use MCP without understanding its technical details. All you need to know is that MCP is a way of linking software tools, sites, and apps to AI platforms like Claude and ChatGPT.

Remember the world prior to USB? Printers, hard drives, cameras, and external monitors had their own special cords to connect to your computer. I just cleaned out dozens of them from a drawer in my Manhattan apartment. Now they’re obsolete because USB ports are everywhere. MCP is a similar unifying standard for linking tools to AI.

5 Ways I’m Using Tools Connected to Claude

Manage Email 📧

I rely on Superhuman Mail to read, organize, and respond to email. It’s fast, easy to use, reliable, and integrates with my calendar. I use it with three distinct email addresses. Because I have to act on important messages, I’ve linked it to Claude.

Get started: The connection guide walks you through linking your email to Claude or ChatGPT. You can then ask your AI assistant to:

* “Help me turn a bunch of starred emails into an afternoon plan.”

* “List important messages I’ve sent this month that the recipient hasn’t yet opened.”

* “Draft concise responses to routine customer questions for my review.”

Some of these tactics will also work with Gmail and Outlook connectors.

Example query: “Look at my five most recent starred emails, suggest an action list for this afternoon based on my priority list, then put an hour on my Google Calendar to act on them.”

Do More with Meeting Notes 🗒️

I use Granola as my notepad during meetings. It transcribes conversations, then creates a summary based on the transcript and my own notes. (See my guide). I can already ask questions about my meetings in Granola without needing a separate AI tool.

But the advantage of linking Granola with Claude (or ChatGPT) is that Claude has access to insights in my notes, email, and Google Drive, so it can integrate the info it pulls from Granola within the context of a broader analysis.

Get started: The Granola MCP guide explains how to link it to your AI. Unlike many other paid services, Granola actually lets free users query meeting notes (for the past 30 days) using your AI tool of choice.

Example query: “Give me a summary of the research questions I said I’d follow up on in my meeting with Pat. Next to each task include a bulleted list of the background details I already collected in my research spreadsheet.”

Edit Images and Videos 🌆

Photoshop and Premiere are powerful but complicated. Now you can edit an image or video without even opening a separate app. Set up the plugin, then tell your AI assistant to use it in your prompt. The AI assistants are often clever enough to figure out which tool to use even if you don’t explicitly mention it.

Get started: Install the Adobe app in ChatGPT. Or add it to Claude, using this guide. Your AI assistant will now have access to the capabilities of Photoshop, Premiere, Firefly, Express, Acrobat, and other Adobe apps. You don’t even need an Adobe account to get started, though it might be helpful to get a free one if you want to organize, improve, and act on your creations later. (Canva’s MCP is also useful).

Example query: “Help me change the text in this graphic.” Or “Reformat this horizontal video clip for YouTube Shorts or Instagram Reels.” Or “Add background blur to this headshot, fix the lighting, and crop it for a portrait.”

As a test, I changed the first line in an illustration from “Bold” to “Kind.” Notice that the first attempt wasn’t perfect. The period after “Kind” was missing. But a quick edit request fixed that. The Photoshop edit preserved the font, style, spacing, and angle.

The benefit: Instead of hunting through Photoshop menus trying to figure out how to do this, I just asked ChatGPT to use Photoshop to make a change. In the long run, being able to use natural language to accomplish tasks like this may shift how we spend our time away from technical menu-hopping toward more creative work. We’ll spend more time thinking about what to do and why, rather than how to technically get it done.

Find Highlights 📚

I use Readwise to collect the passages I highlight when reading online or on my Kindle. It also hosts passages I save when listening to podcasts with the Snipd app.

Get started: The Readwise MCP lets you make use of the highlights you’ve made while working on other projects with an AI assistant.

Example query: “Show me a bunch of my Readwise highlights that include descriptions of desserts, especially from European novels, then gather a list of related recipes I can make with my daughters before our trip.”

Research Legal Cases 🔎

Court Listener from the Free Law Project is a handy way of gathering info about court cases. You can ask for records related to Elon Musk’s recent testimony without paying for a legal research service. Thanks to Hong Qu for the tip.

Get started: Use the Court Listener MCP guide for free with Claude or ChatGPT. First set up a free Court Listener account.

Example query: “Review the news article at XYZ link, find the case that’s being discussed, and give me additional details about the case and any other related recent cases.”

Other Useful MCP Tools 🛠️

* Rize is my favorite tool for time-tracking. I linked it to Claude so I can learn from how I’m spending my time and assess that alongside info from my meetings, email and calendar. The Rize MCP page includes use-cases and helped me get started. Rize requires a paid subscription.

* I use Raindrop to save links I’ll need later. I checked the Raindrop MCP page to set it up and learn about the kinds of queries I can run from Claude. When I’m doing research in a project, for instance, I can ask it to pull in relevant links I’ve saved. Or I can even ask Claude to put the links from a spreadsheet I’m working on into my Raindrop bookmark collection with appropriate tags.

* Sublime is another tool I use to save quotes, images and useful pages online. Unlike Raindrop and other well-designed clipping tools like MyMind, which are fully private, Sublime lets me see related material other people have saved. Now I can ask Claude to pull in relevant material from Sublime.

* Substack has a new MCP, available to select publishers as of now. It lets Claude coach me on my analytics. I recently asked for an analysis of send times to figure out how they impact open and click rates. Substack’s help page notes that the MCP has “read-only access to publication data such as dashboard metrics, traffic data, and publication settings. It cannot publish posts, send Notes, or modify your account.”

How to Link Tools to Your AI Assistant

* Decide what kind of connector will be useful to you.

* Email: Gmail, Outlook, Superhuman, and other email services now let you analyze and respond to your messages.

* Files: Analyze or act on files in your Google Drive, Dropbox, Box, Slack, Notion, or anywhere else you keep your documents and files.

* Planning: Add events to your Google or Outlook calendar, or organize projects with tools like Airtable, Monday, ClickUp, Asana, and Linear.

* Fun: Create Spotify playlists based on your work vibe or search StubHub or SeatGeek for tickets your family or friends might enjoy.

* Pick from your AI tool’s curated list. Claude and ChatGPT each have a bunch of services pre-configured to work. Perplexity now does too. Popular ones include Google Drive, Gmail, Google Calendar, Canva, Figma, and Notion.

* Paste in the address of a custom connector. For tools that are not on the default list, you put in an MCP address, which is like a special website to connect an external service to your AI tool. Find more to try in a directory.

Step by Step

* Click connect on the service you want.

* Log in to that service in the window that opens.

* Approve permissions your AI assistant asks for, so it can access the external tool. Limit permissions to view only if you want your AI to see info from a linked service but not change anything. You can update permissions later in your AI tool’s settings.

Getting started with MCP connections doesn’t require any programming or technical wizardry. If you can add an app to your phone, you can do this. (Note: Google’s Gemini doesn’t yet enable easy MCP connections).

Be Careful About Linking Private Data

Think twice before connecting services that host sensitive info. I haven’t linked my bank accounts to my AI tools, for example. If you do that and someone gets access to your AI account, they’ll be able to find out a lot about your finances.

* It can happen when a thief uses a “prompt injection” to manipulate an AI tool into releasing sensitive info.

* Or it can happen if your phone is lost or stolen. New York, London, Paris, and other major cities see thousands of phones stolen each year (Zipdo 2026 report).

* Data can also leak from AI systems. It’s rare, but there have been cases like this one.

Be Cautious About Letting AI Tools Act on Your Behalf

I’m not yet letting AI tools send emails for me. Or submit forms or applications. If Claude or ChatGPT generates something odd because of a glitch, or because I rushed a query, I want to be the one noticing the error.

When you start connecting AI tools to external services, you have the option to give your AI assistant power to do things on your behalf. That can be useful for research, summarizing meeting notes, or cleaning up messy computer folders.

But you or your AI assistant could make a costly mistake with important info. In a rare but alarming case, Cursor, an AI tool, deleted PocketOS’s company database and its backup (Guardian article). A related 2025 case involved Replit (Fortune article).

Other Ways Connected AI Can Go Wrong

* Travel booking blunder. You ask it to cancel a reservation, and it cancels your entire itinerary. Or you ask it to book a flight on 7/1/27 and it books a nonrefundable ticket on 1/7/27, assuming you were using the European date system and meant January 7, not July 1.

* Disappearing Files. You ask it to get rid of duplicate files. It deletes an entire folder with a similar name.

* Calendar Chaos: You ask it to “find a time for everyone” and it reschedules an existing meeting in the wrong time zone, because you were traveling when you wrote the request.

I haven’t encountered any of these errors. But these services are still new, so you may encounter occasional bugs or blunders.

From Answer Machine to Headquarters

I initially thought of AI tools as answer machines. Ask for info, get back useful text. Then I thought of AI assistants as question machines, provoking me to think about things I hadn’t considered. Now I think of them as my online headquarters.

Claude serves as a dashboard where I can act on my email, notes, documents, calendar, designs, saved links, and meeting transcripts. It’s like having a new partner to support me and help make work a little more efficient and creative.

p.s. To see these connections in action, watch a recording of my live workshop. You’ll find it on the perks page for paid subscribers.

Google’s Pinpoint is now open to everyone. It’s a surprisingly powerful free tool for making sense of giant piles of digital stuff. (Before June 3, it was restricted to journalists and academics). Read on to learn more about creative ways to use Pinpoint; its new AI features and their limitations; and how Pinpoint differs from NotebookLM.

How Pinpoint Works

Pinpoint lets you store and analyze hundreds of thousands of files so you can find tiny needles in gigantic digital haystacks.

* Pinpoint can transcribe hundreds of hours of audio and video.

* It also makes your handwritten text, scans, and PDFs searchable, like my enormous collection of scanned handwritten notes and whiteboards.

* Once Pinpoint processes your files you can search, summarize, and organize your collections.

* Pinpoint makes it easy to query, label, and extract data from hundreds or thousands of documents. It’s simple to use. No complex menus or commands.

Getting Started

* Start by uploading PDFs, emails, audio and video files, handwritten notes, or other file types.

* Each collection can have up to 200,000 files. You can have an unlimited number of collections, which function like folders.

* Journalists and academics can request “Pinpoint for Professionals,” which provides 100GB of storage. Others start with 1GB.

* Audio and video files can be up to 2 hours long and 8GB. The limits are much more generous than what other AI tools, like NotebookLM, offer.

* Pro tip: Create separate Pinpoint accounts for each of your Google accounts. That gives you more storage. It’s also how I keep personal projects separate from work. You can always download files you’ve previously uploaded. And request additional storage if you reach your limit.

Pinpoint Features to Try

* Scour through audio recordings to locate key moments. Pinpoint transcribes in more than 100 languages. Upload and transcribe your recorded presentations to review how you frame a particular topic. Or how water pollution is described in local council meetings.

* Explore text within images and handwritten notes. I’ve scrutinized my old handwritten notes for ideas and checked whiteboard photos for explanations I can improve.

* Share a document collection. Invite individual collaborators or publish a collection for public exploration. Giving readers access to source material can be a valuable form of transparency in journalism.

* Analyze an email or document archive. Assess a public email trove or document collection, like files from the Enron trial, for connections between politicians and companies, or financial impropriety.

* Focus your research on particular people, organizations, locations, or date ranges. Pinpoint automatically lists a collection’s most frequently-mentioned entities. Click on an entity to jump to exactly where it’s mentioned.

* Export important Gmail folders with Google Takeout in .mbox format. Takeout lets you export and back up anything Google hosts. You can then upload your email collection to Pinpoint to find patterns, or locate references to specific people, places, or organizations.

🎁 Try my new Pinpoint Assistant to get personalized ideas for how you can use Pinpoint for a project you’re working on.

Pinpoint in Newsrooms

News organizations have relied on Pinpoint for award-winning investigations involving thousands of documents, including:

* Blind Spot by the Boston Globe (Pulitzer)

* Poisoned by the Tampa Bay Times (Pulitzer)

* Secret Sauce: Expired from North Carolina’s Blue Ridge Public Radio (BPR) (Edward R. Murrow Award).

* Z. Waite’s detailed case study explains how and why BPR used Pinpoint. Waite also notes four good, free, alternative tools: DocumentCloud, Datashare, OpenRefine, and Datasette.

Public Collections

* Pinpoint’s “Explore” section lets you examine document collections from more than 200 news organizations, ranging from The New York Times and The Washington Post to The Hindu and Süddeutsche Zeitung. Test out the searching and filtering features before uploading anything.

* Notable document sets include JFK assassination records, Mueller Court filings, and 80 years of U.S. foreign agent registrations (86,018 documents) uploaded by the Center for Public Integrity.

New AI Capabilities

Pinpoint has a bunch of new AI features in beta available in more than 80 countries. In my testing, not all of the AI capabilities work reliably yet, but you can request early access. Pinpoint’s AI features are designed to help you analyze your files, not generate original content as you might with Gemini or NotebookLM.

* Explain words or phrases in any file. Highlight any text and ask Pinpoint to put it in context. I like the short, useful explanations based on what else is in a document.

* Google words or phrases inside your text to learn more from Google. In my tests, this beta feature consistently yields error messages.

* Summarize Collections. I like how Pinpoint gives me an AI-generated overview of every file I upload. It can also summarize an entire collection.

* Extract data into spreadsheets. Pull info from up to 100 documents at once and deliver it as a sheet, with links back to the source text for each data point. That’s handy for tracking mentions or doing comparative research. Try this feature for analyzing public government contracts or other information in PDF form that would be easier to work with in a spreadsheet.

* Automatically label hundreds of your files in a collection. Let’s say you have a public email dataset. You may want to evaluate just those written by a particular person, or just those discussing a particular stock. Instruct Pinpoint and it will label your collection for you. Limitation: Pinpoint can label 1,000 files at a time. In my tests, the interface only let me select 100 files. If you’re working with tens of thousands of files, labeling may be tedious.

* Transcribe audio quickly. Pinpoint now claims to give you high-quality transcribed text 20x faster than it used to. I couldn’t verify that specific metric, but it’s generally fast. Each file is helpfully time-coded. Click on any section of text to hear the corresponding audio. Limitation: unlike Wispr Flow and Letterly, which I use for my personal dictation, Pinpoint sometimes mangles names, and doesn’t learn from its errors.

* Compare any two or three files. See what changed in multiple versions of a document, or how three different people addressed the same subject.

* Query your collection with ordinary language. Results are often fast, useful, and linked back to the original document. Expect occasional errors, though. One search I tried, for example, returned a document mentioning someone with a similar but different name from the one I was searching for.

* Create a timeline. If you’re looking at how something developed over time, you can pick up to 100 files and generate a timeline. You can optionally specify a topic for the timeline. This might be useful if your dataset has dated transactions, for example, or multiple reports you want to put in order.

Pinpoint vs NotebookLM

* What’s similar: Both NotebookLM and Pinpoint are free Google services that allow you to efficiently summarize and search though large documents.

* What’s different: NotebookLM synthesizes and generates (slides, infographics, video and audio podcasts, and reports). Pinpoint, on the other hand, focuses on finding patterns and organizing a wider array of file types in much larger collections of email, multimedia, and scanned images.

* NotebookLM allows 50 files per notebook for free users. (See my guide). Pinpoint lets you upload 200,000 files into each collection.

* Combine the two: If you have a large collection of documents, consider gathering, storing, organizing, and transcribing in Pinpoint. Then move the most important files into NotebookLM for further analysis and to generate artifacts like reports, slides, infographics, flashcards, audio, and video.

Privacy

* Your documents are private. Nothing you upload is public unless you publish a collection. Read Google’s Pinpoint privacy details.

* Your files are not used to train AI models. Google explicitly notes that documents you upload won’t be used to train Large Language Models. Read Google’s statement.

* The bottom line: I trust Pinpoint for non-sensitive document work. But because uploads are processed on Google’s servers, Pinpoint may not be a fit for everything or everyone. Here are additional privacy details.

Limitations

* No mobile app. You can view docs on a phone browser, but not all features work.

* No NotebookLM integration yet. You can’t easily move files from one service to the other.

* Storage caps. On a 1GB account, you may hit storage limits with large files.

* AI features aren’t error free. No AI implementation is.

I love new gadgets and gizmos, and I’m constantly trying new sites and apps. So I was intrigued by the title of Eric Athas’s upcoming book, Saying No to New.

Eric’s an editor at the New York Times, where he helps journalists make the most of new tools. He’s also a lifelong early adopter. He told me he used to wait in line for new iPhones. But his upcoming book is about thinking twice about new stuff.

In our Substack Live conversation, we talked about old gadgets we still love and new gadgets we never use. Eric shared advice on how to tell the difference between things that might genuinely improve your life, and gizmos that will end up at the back of a closet. We even did a little show and tell with various odd gadgets in our offices.

📺 Watch the full conversation above, or read highlights below.

1. The Vanishing Gap Between Wanting and Getting

When Eric and I were growing up, if you wanted to buy something cool you saw on TV, you’d have to drive to a store. You or your parents would have to spend cash. If you ordered something by mail, you’d wait weeks for delivery.

Today, you can tap on a phone and the thing that caught your eye appears at your door the next day. You can even buy now, pay later, so you don’t need cash. Coming next? AI agents that shop for you proactively. They anticipate what you want so you don’t have to make any decision at all.

Eric calls this the collapse of the “new thing gap.” The time, distance, and cost between seeing something new and acquiring it has shrunk. That gap used to protect us from buying on impulse.

* One-click ordering eliminated distance.

* Free shipping removed the physical effort of the pickup errand.

* Deferred payments eliminated financial friction. You don’t even need the money.

Eric suggests we reintroduce friction by pausing long enough to ask whether the new thing will actually matter a month from now.

2. Show and Tell: Our Gadget Graveyards 🎪

Eric and I compared old odd gadgets in our offices.

From my desk:

* Multiple VR headsets. I have at least three, including one with the plastic still on it. You slot your phone in, close it up, and get an immersive view. Remember when the New York Times announced in 2015 it would ship a million Google Cardboard VR headsets? Eric confirmed that the headset now lives in the Times’s in-house museum.

* Lumo posture band. This posture sensor had a belt that wrapped around my waist and buzzed when I slouched. It was a cool, if weird, concept, but the buzzing was distracting, I still slouch, and the product was discontinued. It’s lived in my drawer for years.

* PLAUD AI recorder next to my brother’s old tape recorder. The old one has a red record button, a play button, and a stop button. You know exactly what to do with it. The Plaud is sleeker but less intuitive.

* Sand timer. This one is both decorative and useful. It’s silent, easy to use for timing, and never needs to be charged. I use it to stay focused during hard tasks.

From Eric’s desk:

* A USB coffee mug warmer. Cracked. Unused. Eric’s take: once you introduce a USB cord into the coffee experience, it loses its magic.

* NeeDoh stress balls. A kid craze. Eric’s children wanted them, squeezed them for a day, and abandoned them. He wrote about the NeeDoh fad here. I have multiple stress balls, and I use them often. Consumer Reports warns they can create a sticky mess or worse.

3. New Things Worth Saying Yes To ✅

Eric’s book isn’t about rejecting everything new. It’s about choosing things thoughtfully so the genuinely useful things don’t get crowded out. Some of the new tools we like:

* Seek app. Free. Point your phone at any plant or animal in nature and learn what it is. I discovered it during the pandemic and still use it regularly.

* Merlin app. Free. Record birdsong and the app identifies the species. Eric and I are both fans.

* Granola. AI meeting summaries. It’s now part of my workflow. Here’s why. It’s infrastructure for me, not novelty. Free for basic transcriptions and summaries. I pay $14/month for additional features, like storing meeting notes for months and querying them with Claude.

What these tools have in common: they solve a real problem, they’ve lasted, and we’ve stuck with them.

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4. Our Brains Chase Seductive Novelty 🧠

Eric’s new book is grounded in neuroscience. When we encounter something new, we get a dopamine hit. That neurological response evolved to help our ancestors survive. New food sources, new paths, new shelter: those discoveries were rewarding.

But sometimes novelty seduces us without offering anything meaningful. In one study Eric described, rats repeatedly crossed an electrified grid just to explore an unfamiliar area. They chose pain plus novelty over a known food source. Humans do something similar. We covet a new phone partly for its camera, but partly just because it’s new. Then we do it all over again. Even if we can’t afford it. That’s one reason why so many Americans are in debt.

I recently read Dopamine Nation, a surprisingly engrossing book by Dr. Anna Lembke, about how our brains are so readily seduced by pleasure.

What results is an unfortunate cycle. We get something new, enjoy it briefly, and soon we’re scanning for the next new thing. My college advisor, Daniel Kahneman, studied and wrote about this “hedonic treadmill” effect.

His research showed that we overestimate how much a new purchase will improve how we feel. And novelty tends to wear off quickly. He called it “hedonic adaptation.”

That doesn’t mean we should avoid all new things. But it does mean we should think carefully about whether there’s something genuinely meaningful behind the new shine.

5. Experiences Outlast Products 🎒

Research shows that trips, cooking classes, concerts, and other new experiences tend to give us more lasting delight than new products do.

That’s partly because experiences tend to be social. You go with someone. Or you meet people there. You talk about it afterwards. Trips have a beginning, middle, and end. You have a story you can retell. A new pan doesn’t generate much conversation after the first week. Its novelty fades fast.

Kahneman, who was one of the best teachers and advisors I’ve ever had, introduced me to the related “comforts vs. pleasure” theory. It was originally described by Tibor Scitovsky in The Joyless Economy: The Psychology of Human Satisfaction. It changed the way I think about spending money.

Comforts are things we buy and then quickly adapt to. A nicer couch. A bigger TV. They feel great at first, then they fade into the background.

Pleasures, on the other hand, are transient experiences: a delicious dinner with friends, a live concert, surprise flowers, or a summer walk with someone you love in a new city.

These kinds of experiences are brief, but they retain their emotional charge when you reflect back on them. Kahneman’s argument, supported by numerous studies, was that pleasures enhance happiness more durably than comforts, because we don’t adapt to them. The research findings’ bottom line: if you want more happiness, splurge on special experiences with loved ones rather than expensive things.

Eric’s suggestion: if you’re drawn to something new, try turning the purchase into a social experience. Waiting in line with a friend for trendy cookies transforms a dopamine-seeking buying excursion into an experience and a fun shared memory.

Daniel Pink recently made a compelling video on the same theme: how to spend money so it actually makes you happier. His take aligns with Eric’s and Kahneman’s. Spend on experiences, not things.

6. Ask These Questions 🔍

Eric suggests a few questions to ask before you acquire something new:

* Will I still use this in a month? Will this serve an ongoing purpose, or will it get stuck in the background? (I’ll use this one the next time I’m tempted by a kitchen gadget or iPhone app).

* Is it intuitive to use? Eric points to modern car dashboards as a cautionary tale: touchscreens that look futuristic can end up being more confusing than the knobs and buttons they replaced.

* Is it likely to distract you? A sand timer, a paper book, a physical photograph: these do one thing well without pinging you. A single-purpose app on your phone, on the other hand, puts you one swipe away from email, Instagram, and other Internet rabbit holes.

7. Good Enough is Sometimes Enough 👍

Eric’s coffee maker still works. His wife wants him to upgrade. He resists, not out of stubbornness, but because it does exactly what he needs. He programs it at night. He wakes up to fresh coffee. No learning curve.

His suggestion: before replacing something, ask whether what you already have is still good enough. Something better always exists, but if the upgrade is just about novelty, it might not be worth the effort, expense, or space.

I have more than 600 apps on my phone. I use only a small fraction regularly. But I’ve realized that going back and manually deleting everything I’m not using is a waste of time. In the digital domain, unlike the physical one, unused things don’t take up much space. Going back and deleting emails or apps one by one feels like more of a waste than letting them sit idly in the graveyard.

8. Paper Books and Quiet Treasures 📖

About two-thirds of Americans still read books on paper despite the convenience of ebooks. Part of what’s appealing about them is sensory: the way pages turn, the way a book feels in your hands, the smell of the paper.

But there’s another advantage. A paper book doesn’t send notifications. It offers no tempting apps. The same goes for vinyl records, Polaroid photos, sand timers, and handwritten journals. Each of these enables you to deeply focus on what you’re doing.

My grandfather taught me to use a Minolta camera when I was little. The quality of its pictures doesn’t match that of an iPhone. But old objects like the Minolta have intrinsic value beyond their function. A hand-me-down camera is a reminder of love.

I have more than 50,000 photos on my phone. That abundance, paradoxically, devalues each individual image. When film was limited and developing took days, every picture felt more precious. Anticipating which pictures might turn out was part of the thrill of photography. I don’t want to return to that era. But the photos my wife and I have printed and framed mean more to me than many of the ones sitting in my phone’s camera roll.

9. Choices Are Contagious 😷

The last chapter in Eric’s book is about invisible influence. If your friends are constantly upgrading their homes, devices, or apps, you might feel the pull to keep pace. It’s tempting to follow the cultural lead of those around us.

The reverse is also true. Choosing to stick to what you have quietly signals to other people that it’s okay to keep the old thing, to skip the trend.

Read more 📚

* Saying No to New Available for pre-order. Out September 15 from Balance.

* Eric Athas on Substack Behind-the-scenes updates, pre-order bonuses, and a decision-making tool tied to the book’s ideas.

* Dopamine Nation by Dr. Anna Lembke. The neuroscience of novelty-seeking. Eric and I both referenced it.

* The Joyless Economy by Tibor Scitovsky. A psychology classic about what impacts happiness and how comforts differ from pleasures.

What’s a new thing you say no to? Leave a comment 👇

Thank you Des Kennedy, Betty Solomon, George K Thomas, and many others for tuning into my live video with Eric Athas and thanks to you, reader, for making it all the way down here to the end of this post.